WO2008116385A1 - Dérivés d'acide caféyl quinique contenant de l'azote, et procédé de préparation, composition pharmaceutique et leur utilisation - Google Patents
Dérivés d'acide caféyl quinique contenant de l'azote, et procédé de préparation, composition pharmaceutique et leur utilisation Download PDFInfo
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- WO2008116385A1 WO2008116385A1 PCT/CN2008/000562 CN2008000562W WO2008116385A1 WO 2008116385 A1 WO2008116385 A1 WO 2008116385A1 CN 2008000562 W CN2008000562 W CN 2008000562W WO 2008116385 A1 WO2008116385 A1 WO 2008116385A1
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- hydrate
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- CWVRJTMFETXNAD-NXLLHMKUSA-N trans-5-O-caffeoyl-D-quinic acid Chemical class O[C@H]1[C@H](O)C[C@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-NXLLHMKUSA-N 0.000 title abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title 2
- 229910052757 nitrogen Inorganic materials 0.000 title 1
- 238000006902 nitrogenation reaction Methods 0.000 title 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
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- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 6
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
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- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003277 amino group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
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- 229960002555 zidovudine Drugs 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- Another object of the present invention is also a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of the above compound or a salt thereof or a hydrate thereof, and a pharmaceutically acceptable carrier.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des dérivés d'acide caféyl quinique et leur procédé de préparation, une composition pharmaceutique les contenant et leur utilisation pour le traitement ou la prophylaxie de la virose, en particulier l'utilisation pour le traitement ou la prophylaxie du virus syncytial respiratoire et du virus de l'hépatite B, qui présente des avantages de sécurité, d'efficacité élevée et de faible toxicité.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/532,763 US8722725B2 (en) | 2007-03-23 | 2008-03-21 | Caffeoylquinic acid derivatives containing nitrogen, and preparation method, pharmaceutical composition and usage thereof |
EP08715014.0A EP2128125B1 (fr) | 2007-03-23 | 2008-03-21 | Dérivés d'acide caféyl quinique contenant de l'azote, et procédé de préparation, composition pharmaceutique et leur utilisation |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200710086601.9 | 2007-03-23 | ||
CN200710086601 | 2007-03-23 | ||
CN2008100843914A CN101284799B (zh) | 2007-03-23 | 2008-03-20 | 咖啡酰奎宁酸含氮衍生物及其制备方法和其药物组合物及用途 |
CN200810084391.4 | 2008-03-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008116385A1 true WO2008116385A1 (fr) | 2008-10-02 |
Family
ID=39788039
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2008/000562 WO2008116385A1 (fr) | 2007-03-23 | 2008-03-21 | Dérivés d'acide caféyl quinique contenant de l'azote, et procédé de préparation, composition pharmaceutique et leur utilisation |
Country Status (4)
Country | Link |
---|---|
US (1) | US8722725B2 (fr) |
EP (1) | EP2128125B1 (fr) |
CN (1) | CN101284799B (fr) |
WO (1) | WO2008116385A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2008323683B2 (en) * | 2007-11-09 | 2014-10-02 | University Of Tennessee Research Foundation | Anti-inflammatory quinic acid derivatives for oral administration |
WO2023212353A1 (fr) * | 2022-04-29 | 2023-11-02 | Emory University | Inhibiteurs de l'entrée de virus dérivés de plantes |
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CN101284799B (zh) | 2007-03-23 | 2013-04-03 | 浙江医药股份有限公司新昌制药厂 | 咖啡酰奎宁酸含氮衍生物及其制备方法和其药物组合物及用途 |
CN101397333A (zh) * | 2007-09-27 | 2009-04-01 | 浙江医药股份有限公司新昌制药厂 | 去羟基万古霉素及其制备方法、和其药物组合物及其用途 |
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US9126968B2 (en) * | 2013-06-13 | 2015-09-08 | National Applied Research Laboratories | Quinic acid derivative, process for preparation and uses thereof |
CN104761464B (zh) * | 2014-01-03 | 2017-08-04 | 陈惠民 | 一种奎尼酸衍生物、其制程及其用途 |
CN104644711B (zh) * | 2014-11-21 | 2018-05-22 | 暨南大学 | 一种艾纳香属植物提取物及其制备方法与应用 |
CN105130838A (zh) * | 2015-07-15 | 2015-12-09 | 遵义医学院 | 一种绿原酸酰胺衍生物及其合成、应用 |
FR3050455B1 (fr) | 2016-04-26 | 2019-06-14 | Temisis | Derives amides des acides polycafeoylquiniques, procede de preparation et utilisations |
CN111423407B (zh) * | 2019-01-10 | 2021-06-08 | 中国医学科学院药用植物研究所 | 一种咖啡酰奎宁酸类衍生物及其制备方法和用途 |
CN110156628B (zh) * | 2019-06-19 | 2022-05-17 | 暨南大学 | 一种环三醇衍生物及其制备方法与应用 |
CN110218160B (zh) * | 2019-06-19 | 2022-05-24 | 暨南大学 | 一种奎宁酸衍生物及其制备方法与应用 |
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Publication number | Priority date | Publication date | Assignee | Title |
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AU2008323683B2 (en) * | 2007-11-09 | 2014-10-02 | University Of Tennessee Research Foundation | Anti-inflammatory quinic acid derivatives for oral administration |
WO2023212353A1 (fr) * | 2022-04-29 | 2023-11-02 | Emory University | Inhibiteurs de l'entrée de virus dérivés de plantes |
Also Published As
Publication number | Publication date |
---|---|
EP2128125B1 (fr) | 2015-05-06 |
EP2128125A1 (fr) | 2009-12-02 |
CN101284799A (zh) | 2008-10-15 |
EP2128125A4 (fr) | 2010-03-31 |
US20100144828A1 (en) | 2010-06-10 |
CN101284799B (zh) | 2013-04-03 |
US8722725B2 (en) | 2014-05-13 |
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